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The First Date and sex with a Ladyboy

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Are you going out on a date for the very first time with a ladyboy ? Are your nerves unstoppable and your neurons have left the building? Calm down Bruce, I will help you find a way in dealing with your first ladyboy date. I’m a ladyboy myself and if that’s not enough to pacify your anxiety, I don’t know what will.

Please take these tips with a grain of salt because we all have different individualities. I’m assuming that you’re going out on a date with a transgender woman from Asia because you’re in an article that uses the ladyboy term that is widely used in the east. I’m from the Philippines and I’m going to share with you 3 key topics that are of paramount importance in most Asian women’s lives.

First Ladyboy Date



big ladyboy family

I cannot stress enough of how important it is for you to be family-oriented when you’re dating an Asian ladyboy.

We, most of the time, put our family, most especially our parents, above ourselves.

If you’re going to be dating a ladyboy from Asia, you have to be prepared to love her mother, father, brother, sister, and down to her very last 3rd cousin.

It’s inevitable that you’ll be regularly invited to tag along with your future ladyboy girlfriend in family affairs so once you’re in your romantic date, you have to let her know verbally that family ties matter.


monogamy with ladyboy

I’m not saying that western people are all in an open relationship so please don’t attack me.

It’s just that from my experience, most of the American guys I’ve dated are more than willing to exercise their infidelity.

Monogamy is not reaching for the stars and if you’re looking into turning your ladyboy date into a wife, you have to have a strong stance with this issue.

Tell her that you’re not into threesomes and cheating and you want a love that’s only exclusive for 2 that’s hopefully going to last a lifetime. Not only will she be smitten, but she might also be able to feel love at first sight. Remember, your goal is not only to leave her besotted, but you must also beguile her.

Pay for the Damn Bill

dating with ladyboy

I’m a very independent woman but if you’re not going to foot the bill on the first date which YOU invited me on, I will play TLC’s “No Scrubs” in full volume while we’re in a quaint restaurant while taking the cash out of my wallet.

This is pretty much common sense but I’m just here to remind you that this behavior isn’t cute.

Even if the date didn’t turn out well, still pay for the bill you jerk. Anyway, these are just a few things of what you must remember when you’re on the first date with a ladyboy. Have a great time and remember to not get too drunk. Keep yourself together Bobby.

First Ladyboy Sex

couple first time sex

Now that we’ve discussed dating ladyboys for the first time, it’s very important for you to know what happens in the area when it comes to finally having sex with your ladyboy date.

I’m going to divide this into 2 sections based on 2 points of view. The first one will be from my interview with a ladyboy friend and the 2nd one, from my interview with a gentleman.

Ladyboys on First-timer Gentlemen

You’re probably a guy who’s reading this and every fiber of your being is going awry. The thought of having first time sex with ladyboys can prove to be an impalpable feeling. It’s totally understandable but before doing the actual deed, don’t just dive your way into it.

There are things that you have to remember before getting yourself involved in this situation. There are caveats to consider so be wary that it’s not all fun and games.

The Ladyboy who Dislikes her Penis

ladyboy dislikes

You see, not all ladyboys are open to the fact that most men who want to have sex with them are interested in their penises.

Some ladyboys think that men who are into them aren’t interested in the girl toy.

Most lack education in knowing that there are men who are straight but are into penises while some have heightened levels of gender dysphoria that they can’t stand what they have between their legs.

My friend Patricia, who’s now a proud owner of a neovagina, never had her penis involved in the mix. She was never comfortable even looking at it, let alone have a man touch it. You may come across ladyboys who are like this so be quite verbal before the first night.

Don’t string someone along just because you want to get into her knickers. Besides, you’re not even going to truly get what you want even if she finally agrees to have sex with you. If you want your first time sex with a ladyboy to go as how you’d expect it to, communication is key.

The Ladyboy who Likes her Penis

ladyboy in lingerie

Let’s head on to the other kind of ladyboy; the one that I’m banking on to be more in tune with your preferences.

She’s the type who has no issues utilizing her penis in making love.

She’s probably also the reason why you signed up on a ladyboy dating website.

Albeit her comfort level when it comes to what she has between her legs, you must remember that she might not be fully functional because of hormone replacement therapy (HRT). Most ladyboys take this type of medication. While they have no qualms in having you feast on what they possess, they might not be as gifted with virility as you do.

Ladyboy dating can be quite complicated. It’s not as easy as regular dating and thinking of which hole to use for the week. Never get your expectations to fly too high is all that I’m saying.

The Fully Functional Ladyboy

ladyboy licks

I’m guessing that she’s the type that you’re truly looking for and she’s actually what your wet dreams are made of.

You see, I’m a ladyboy and most of my friends aren’t fully functional.

This type of ladyboy is quite rare but the porn industry makes novices think that she’s the norm.

The Fully Functional ladyboy is someone who wants, knows, and enjoys her penis and she’s unapologetic about it. However, one caveat about her is that she may not be into switching so if you’re going to date her and you want to get the best of both worlds, ask her if she’s versatile.

Pure top ladyboys exist and if you do not discuss this with her in the early stages of your dates, you may put yourself in a relationship wherein you’re always in the receiving end.

A Ladyboy’s sexperience with a Virgin

Now, let’s get into the topic of why you’re here. I’ve interviewed a colleague about her first time with a virgin guy (virgin to ladyboys) and his first time with a ladyboy. Let’s call her Fanny to protect her identity.

Fanny’s quite a looker and she’s how you’d describe how a prototype ladyboy fantasy would look like. She has beautiful tan skin, silky long hair, pretty eyes, and a petite yet athletic body. Suffice to say, she could be a model.

I asked her how her experience with a virgin was and she told me that she thoroughly enjoyed it. The reason being is because of the 2 main things that I’ll be listing below.

Ladyboy sexperience

The guy who had sex with her didn’t approach the situation like most men would when it comes to their first ladyboy sex.

He did not just undress and have his ladyboy partner do all the work.

He was willing and he was curious. Topping, bottoming, sucking, rimming, etc.

all constitute having a great first time experience in having sex with a ladyboy. If you don’t know what these are, feel free to look them up in porn.

Fanny told me that this guy did everything and albeit she had to correct her from time-to-time because his only reference was porn, they still had a fantastic time. So much so that they did the deed more than once in just one night.

first time sex with ladyboy

She added that most first-timers were verbal about asking for guidance;

from how to properly suck a penis, wash their anus for bottoming, proper rhythm, sex positions, and more.

No, this will not make your first sex with a ladyboy seem rehearsed, think of it as a sexy student and teacher fantasy.

Fanny added that these 2 things are great factors as to why the men who had their virginity taken by her, truly enjoyed their first ladyboy experience. If you don’t consider open-mindedness and guidance, your first time with a ladyboy might become awkward.

A Gentleman’s First Ladyboy Sex

Now that we’ve sorted out the POV of the ladyboy, let’s discuss something that’s more relatable to you; the point of view of the man who’s about to have his first ladyboy sexual experience.

Because here in My Ladyboy Date, we’re quite open-minded, I know a lot of people who are willing to share their sexual experiences. I’ve interviewed a male colleague about his first time with a ladyboy and I was actually surprised by the situation.

Let’s call him Caesar because I think that it’s a very relevant name for this topic; ladyboy sex being Egypt. Caesar’s discovery of Egypt, I mean, ladyboy porn, started at a very early age. So much so that his actual first sex with a ladyboy was when he was 18 and the latter being 30 !

Caesar’s First Sex with a Ladyboy

first time with a ladyboy

His first sexual experience with a ladyboy comes from a time and country whereby ladyboys were still of taboo. Because of this, most ladyboys at that time had enhanced levels of gender dysphoria. A lot of them are uneducated about the fact that it’s truly possible for a man to prefer a woman with a penis.

He was only a little more than half her age but he was already open-minded about the experience. They met online, went for a drink, and came to her place; only for him to later find out that she was reluctant in using her penis.

Caesar told me that his first time felt too “mechanical”; and it was quite the opposite of what he imagined it to be and what he saw in porn. He said that his partner had mental issues including depression and anxiety, driven by gender dysphoria.

He mentioned that it was an antipode to what he experienced when he started traveling to Asia. Since countries like Thailand and the Philippines were more tolerant back then, he was able to fulfill his fantasies.

What you Should Do on Your First Ladyboy Sex

For you to have a great first time sex with a ladyboy, It’s very important for you to COMMUNICATE. Ample dating is required for this communication to flow in a more natural manner; without her, feeling like you’re only interested in getting to unravel her underwear.

If you practice communication, open-mindedness, patience, willingness to be guided, and respect, your fantasies and virginity will be rewarded in the most memorable way!



Posted in Love & dating

About the author

Amanda Valentine Dela Cruz
Just a random trans woman playing with makeup and skincare. Loves bacon and the operating table. I'm also the author of the dating guide book Dating Transgender Women for Gentlemen. Know more ->

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